CA2700287A1 - Biaryl sulfonamide derivatives - Google Patents
Biaryl sulfonamide derivatives Download PDFInfo
- Publication number
- CA2700287A1 CA2700287A1 CA2700287A CA2700287A CA2700287A1 CA 2700287 A1 CA2700287 A1 CA 2700287A1 CA 2700287 A CA2700287 A CA 2700287A CA 2700287 A CA2700287 A CA 2700287A CA 2700287 A1 CA2700287 A1 CA 2700287A1
- Authority
- CA
- Canada
- Prior art keywords
- ylmethyl
- phenyl
- methanesulfonyl
- benzenesulfonamide
- thiophen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 Biaryl sulfonamide Chemical class 0.000 title claims abstract description 52
- 229940124530 sulfonamide Drugs 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 102000004311 liver X receptors Human genes 0.000 claims abstract description 61
- 108090000865 liver X receptors Proteins 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 201000010099 disease Diseases 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical group 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 206010012601 diabetes mellitus Diseases 0.000 claims description 19
- 210000004185 liver Anatomy 0.000 claims description 19
- 238000011321 prophylaxis Methods 0.000 claims description 19
- 230000001225 therapeutic effect Effects 0.000 claims description 18
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
- 108010023302 HDL Cholesterol Proteins 0.000 claims description 17
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 16
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 16
- 208000002780 macular degeneration Diseases 0.000 claims description 16
- 230000003143 atherosclerotic effect Effects 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 150000002632 lipids Chemical class 0.000 claims description 13
- 108010028554 LDL Cholesterol Proteins 0.000 claims description 12
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 208000027866 inflammatory disease Diseases 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 208000035473 Communicable disease Diseases 0.000 claims description 10
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 10
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 10
- 229940125388 beta agonist Drugs 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 206010008635 Cholestasis Diseases 0.000 claims description 9
- 206010016654 Fibrosis Diseases 0.000 claims description 9
- 238000008214 LDL Cholesterol Methods 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 206010033645 Pancreatitis Diseases 0.000 claims description 9
- 201000004681 Psoriasis Diseases 0.000 claims description 9
- 206010040047 Sepsis Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 230000007870 cholestasis Effects 0.000 claims description 9
- 231100000359 cholestasis Toxicity 0.000 claims description 9
- 230000003920 cognitive function Effects 0.000 claims description 9
- 206010009887 colitis Diseases 0.000 claims description 9
- 230000004761 fibrosis Effects 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000001771 impaired effect Effects 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 208000017520 skin disease Diseases 0.000 claims description 7
- GTFWZYPDNQQBNC-UHFFFAOYSA-N 2-chloro-n-[[2-fluoro-4-(3-methylsulfonylphenyl)phenyl]methyl]-n-(2-methylpropyl)benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(C(=C1)F)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 GTFWZYPDNQQBNC-UHFFFAOYSA-N 0.000 claims description 6
- UFOZSRIERDHISO-UHFFFAOYSA-N 2-cyano-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(C#N)C=1S(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 UFOZSRIERDHISO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- FTDKMMHPVNNKMT-UHFFFAOYSA-N n-(cyclopropylmethyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC3CC3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 FTDKMMHPVNNKMT-UHFFFAOYSA-N 0.000 claims description 6
- LKLDMJSZLOPVMF-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-n-[[3-(3-methylsulfonylphenyl)phenyl]methyl]propane-2-sulfonamide Chemical compound C=1C=CC=C(F)C=1CN(S(=O)(=O)C(C)C)CC(C=1)=CC=CC=1C1=CC=CC(S(C)(=O)=O)=C1 LKLDMJSZLOPVMF-UHFFFAOYSA-N 0.000 claims description 6
- ZOBGTDRMCIQTOA-UHFFFAOYSA-N n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-n-propan-2-yl-2-(trifluoromethyl)benzenesulfonamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1S(=O)(=O)N(C(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 ZOBGTDRMCIQTOA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- OWGWPFQZCIAILM-UHFFFAOYSA-N 1,1,1-trifluoro-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]methanesulfonamide Chemical compound S1C(CN(CC(C)C)S(=O)(=O)C(F)(F)F)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 OWGWPFQZCIAILM-UHFFFAOYSA-N 0.000 claims description 5
- NXIGEVAWKOIAIH-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)pyridin-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(N=C1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 NXIGEVAWKOIAIH-UHFFFAOYSA-N 0.000 claims description 5
- QETBTKCITKPTJN-UHFFFAOYSA-N 2-fluoro-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(F)C=1S(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 QETBTKCITKPTJN-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- FJFRAGLGJABKCH-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[2-(3-methylsulfonylphenyl)-1,3-thiazol-5-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(S1)=CN=C1C1=CC=CC(S(C)(=O)=O)=C1 FJFRAGLGJABKCH-UHFFFAOYSA-N 0.000 claims description 4
- VMOWRQBIANUUOH-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[2-(3-methylsulfonylphenyl)pyridin-4-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(C=1)=CC=NC=1C1=CC=CC(S(C)(=O)=O)=C1 VMOWRQBIANUUOH-UHFFFAOYSA-N 0.000 claims description 4
- PQVUKUBEVAIEEW-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[4-(3-sulfamoylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(SC=1)=CC=1C1=CC=CC(S(N)(=O)=O)=C1 PQVUKUBEVAIEEW-UHFFFAOYSA-N 0.000 claims description 4
- OAIGZCCCTUDHJB-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[4-(5-methylsulfonylpyridin-3-yl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(SC=1)=CC=1C1=CN=CC(S(C)(=O)=O)=C1 OAIGZCCCTUDHJB-UHFFFAOYSA-N 0.000 claims description 4
- JISZLXOVKOMURZ-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 JISZLXOVKOMURZ-UHFFFAOYSA-N 0.000 claims description 4
- RRZZKTQHNFXVGM-UHFFFAOYSA-N 3-chloro-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC(Cl)=CC=1S(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 RRZZKTQHNFXVGM-UHFFFAOYSA-N 0.000 claims description 4
- GIEHGRQOQPVCJR-UHFFFAOYSA-N 5-chloro-2-methoxy-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)N(CC(C)C)CC1=CC=C(C=2C=C(C=CC=2)S(C)(=O)=O)S1 GIEHGRQOQPVCJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005620 boronic acid group Chemical group 0.000 claims description 4
- TWTFWUOWDUNQOZ-UHFFFAOYSA-N n,n-diethyl-2-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl-[2-(trifluoromethyl)phenyl]sulfonylamino]acetamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1S(=O)(=O)N(CC(=O)N(CC)CC)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 TWTFWUOWDUNQOZ-UHFFFAOYSA-N 0.000 claims description 4
- JSLQBPBDJQZBRQ-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-n-[[2-(3-methylsulfonylphenyl)-1,3-thiazol-5-yl]methyl]benzamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(C(=O)C=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)Cl)=CN=2)=C1 JSLQBPBDJQZBRQ-UHFFFAOYSA-N 0.000 claims description 4
- UUHKOANREMIBGE-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(C(=O)C=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)Cl)=CC=2)=C1 UUHKOANREMIBGE-UHFFFAOYSA-N 0.000 claims description 4
- QYYIDQDZYINUIV-UHFFFAOYSA-N n-(2-methylpropyl)-n-[[3-(3-methylsulfonylphenyl)phenyl]methyl]propane-2-sulfonamide Chemical compound CC(C)CN(S(=O)(=O)C(C)C)CC1=CC=CC(C=2C=C(C=CC=2)S(C)(=O)=O)=C1 QYYIDQDZYINUIV-UHFFFAOYSA-N 0.000 claims description 4
- PDAASAKPBNZZQB-UHFFFAOYSA-N n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-1-phenylmethanesulfonamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 PDAASAKPBNZZQB-UHFFFAOYSA-N 0.000 claims description 4
- YJIWTZUCPLKHFT-UHFFFAOYSA-N n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]butane-1-sulfonamide Chemical compound S1C(CN(CC(C)C)S(=O)(=O)CCCC)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 YJIWTZUCPLKHFT-UHFFFAOYSA-N 0.000 claims description 4
- PJJVUXPPSPDNHN-UHFFFAOYSA-N n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 PJJVUXPPSPDNHN-UHFFFAOYSA-N 0.000 claims description 4
- JGFQDFOUEYWLQP-UHFFFAOYSA-N n-(3-chlorophenyl)sulfonyl-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(C(=O)C=3C=CC=CC=3)S(=O)(=O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 JGFQDFOUEYWLQP-UHFFFAOYSA-N 0.000 claims description 4
- INQJFAAPANYNJA-UHFFFAOYSA-N n-(cyclobutylmethyl)-n-[[3-(3-methylsulfonylphenyl)phenyl]methyl]propane-2-sulfonamide Chemical compound C=1C=CC(C=2C=C(C=CC=2)S(C)(=O)=O)=CC=1CN(S(=O)(=O)C(C)C)CC1CCC1 INQJFAAPANYNJA-UHFFFAOYSA-N 0.000 claims description 4
- KNYGWSNCGANEQA-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC=3C(=CC=CC=3)F)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 KNYGWSNCGANEQA-UHFFFAOYSA-N 0.000 claims description 4
- RCMVSTGQJDUTMW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[[3-(3-methylsulfonylphenyl)phenyl]methyl]propane-2-sulfonamide Chemical compound C=1C=CC(C=2C=C(C=CC=2)S(C)(=O)=O)=CC=1CN(S(=O)(=O)C(C)C)CC1=CC=C(F)C=C1 RCMVSTGQJDUTMW-UHFFFAOYSA-N 0.000 claims description 4
- JLTYIXVSDQHHKK-UHFFFAOYSA-N n-[[3-(3-methylsulfonylphenyl)phenyl]methyl]-n-propylpropane-2-sulfonamide Chemical compound CCCN(S(=O)(=O)C(C)C)CC1=CC=CC(C=2C=C(C=CC=2)S(C)(=O)=O)=C1 JLTYIXVSDQHHKK-UHFFFAOYSA-N 0.000 claims description 4
- RDSAYJDHNXZWAK-UHFFFAOYSA-N n-[[4-[3-(tert-butylsulfamoyl)phenyl]thiophen-2-yl]methyl]-2-chloro-n-(2-methylpropyl)benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(SC=1)=CC=1C1=CC=CC(S(=O)(=O)NC(C)(C)C)=C1 RDSAYJDHNXZWAK-UHFFFAOYSA-N 0.000 claims description 4
- XOBSLHQQNQSDAM-UHFFFAOYSA-N n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-n-(2-pyrrolidin-1-ylethyl)-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CCN3CCCC3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 XOBSLHQQNQSDAM-UHFFFAOYSA-N 0.000 claims description 4
- FIKFECVJUVLBHD-UHFFFAOYSA-N n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-n-(oxolan-2-ylmethyl)-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC3OCCC3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 FIKFECVJUVLBHD-UHFFFAOYSA-N 0.000 claims description 4
- FJOHTGPJPBWBMK-UHFFFAOYSA-N n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-n-propyl-2-(trifluoromethyl)benzenesulfonamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1S(=O)(=O)N(CCC)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 FJOHTGPJPBWBMK-UHFFFAOYSA-N 0.000 claims description 4
- VCYRHRFPJWOLQO-UHFFFAOYSA-N n-benzyl-2-chloro-n-[[2-(3-methylsulfonylphenyl)-1,3-thiazol-5-yl]methyl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)Cl)=CN=2)=C1 VCYRHRFPJWOLQO-UHFFFAOYSA-N 0.000 claims description 4
- CRZPCEAXODFDLT-UHFFFAOYSA-N n-benzyl-2-chloro-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)Cl)=CC=2)=C1 CRZPCEAXODFDLT-UHFFFAOYSA-N 0.000 claims description 4
- SZKDAVUZQWPJFX-UHFFFAOYSA-N n-benzyl-3-chloro-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 SZKDAVUZQWPJFX-UHFFFAOYSA-N 0.000 claims description 4
- NCHMRJCDAJQGCU-UHFFFAOYSA-N n-benzyl-n-[[5-(3-methylsulfonylphenyl)-1,3,4-oxadiazol-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2OC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=NN=2)=C1 NCHMRJCDAJQGCU-UHFFFAOYSA-N 0.000 claims description 4
- FZOWRPWZFGSAGP-UHFFFAOYSA-N n-benzyl-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 FZOWRPWZFGSAGP-UHFFFAOYSA-N 0.000 claims description 4
- WBKTXVVQBGTJDW-UHFFFAOYSA-N n-benzyl-n-[[5-[3-(methanesulfonamido)phenyl]thiophen-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2SC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 WBKTXVVQBGTJDW-UHFFFAOYSA-N 0.000 claims description 4
- NLDOCDWHNYIGKV-UHFFFAOYSA-N n-benzyl-n-[[5-[4-(hydroxymethyl)-3-methylsulfonylphenyl]thiophen-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(CO)C(S(=O)(=O)C)=CC(C=2SC(CN(CC=3C=CC=CC=3)S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)=C1 NLDOCDWHNYIGKV-UHFFFAOYSA-N 0.000 claims description 4
- DXGZGWPWFOKHDS-UHFFFAOYSA-N n-methyl-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1S(=O)(=O)N(C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 DXGZGWPWFOKHDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005551 pyridylene group Chemical group 0.000 claims description 4
- LFFAPAQTIMRUFT-UHFFFAOYSA-N tert-butyl 2-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl-[2-(trifluoromethyl)phenyl]sulfonylamino]acetate Chemical compound C=1C=CC=C(C(F)(F)F)C=1S(=O)(=O)N(CC(=O)OC(C)(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 LFFAPAQTIMRUFT-UHFFFAOYSA-N 0.000 claims description 4
- BMBVIUSKDXLZPF-UHFFFAOYSA-N 2,6-dichloro-n-(2-methylpropyl)-n-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound ClC=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 BMBVIUSKDXLZPF-UHFFFAOYSA-N 0.000 claims description 3
- RANRWAZMBKWWIP-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[3-(3-methylsulfonylphenyl)phenyl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(C=1)=CC=CC=1C1=CC=CC(S(C)(=O)=O)=C1 RANRWAZMBKWWIP-UHFFFAOYSA-N 0.000 claims description 3
- GBSGAKFDDQPLFL-UHFFFAOYSA-N 2-chloro-n-(2-methylpropyl)-n-[[4-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC(C)C)CC(SC=1)=CC=1C1=CC=CC(S(C)(=O)=O)=C1 GBSGAKFDDQPLFL-UHFFFAOYSA-N 0.000 claims description 3
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- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
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- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP07117437.9 | 2007-09-27 | ||
EP07117437 | 2007-09-27 | ||
PCT/EP2008/062414 WO2009040289A2 (en) | 2007-09-27 | 2008-09-18 | Biaryl sulfonamide derivatives |
Publications (1)
Publication Number | Publication Date |
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CA2700287A1 true CA2700287A1 (en) | 2009-04-02 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2700287A Abandoned CA2700287A1 (en) | 2007-09-27 | 2008-09-18 | Biaryl sulfonamide derivatives |
Country Status (10)
Country | Link |
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US (1) | US8039493B2 (ja) |
EP (1) | EP2205556A2 (ja) |
JP (1) | JP5307143B2 (ja) |
KR (1) | KR101240809B1 (ja) |
CN (1) | CN101808983B (ja) |
AU (1) | AU2008303601A1 (ja) |
BR (1) | BRPI0817262A2 (ja) |
CA (1) | CA2700287A1 (ja) |
MX (1) | MX2010003224A (ja) |
WO (1) | WO2009040289A2 (ja) |
Families Citing this family (18)
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EP2429995B1 (en) | 2009-05-15 | 2014-01-22 | Novartis AG | Aryl pyridine as aldosterone synthase inhibitors |
JP2013542183A (ja) | 2010-09-07 | 2013-11-21 | エスエヌユー アールアンドディービー ファウンデーション | セスタテルペン化合物およびこれらの物質の用途 |
JP2013542973A (ja) * | 2010-11-22 | 2013-11-28 | ノスシラ、ソシエダッド、アノニマ | 神経変性疾患または神経変性状態を治療するためのビピリジンスルホンアミド誘導体 |
US20130190356A1 (en) * | 2011-12-22 | 2013-07-25 | Genentech, Inc. | Benzyl sulfonamide derivatives as rorc modulators |
AU2013222345B2 (en) | 2012-02-22 | 2017-09-07 | Sanford-Burnham Medical Research Institute | Sulfonamide compounds and uses as TNAP inhibitors |
EP4218935A1 (en) | 2012-08-13 | 2023-08-02 | The Rockefeller University | Lxrbeta agonist for the treatment of cancer |
WO2014085453A2 (en) * | 2012-11-29 | 2014-06-05 | The Scripps Research Institute | Small molecule lxr inverse agonists |
CN104684891A (zh) * | 2012-12-10 | 2015-06-03 | 弗·哈夫曼-拉罗切有限公司 | 作为RORc调节剂的苄基磺酰胺衍生物 |
CA3010883A1 (en) | 2016-01-11 | 2017-07-20 | The Rockefeller University | Methods for the treatment of myeloid derived suppressor cells related disorders |
WO2017223514A1 (en) * | 2016-06-24 | 2017-12-28 | Saint Louis University | Lxr inverse agonists for treatment of cancer |
UY37659A (es) | 2017-04-10 | 2018-10-31 | Phenex Fxr Gmbh | Moduladores del receptor x del hígado (lxr) |
CA3078981A1 (en) | 2017-11-21 | 2019-05-31 | Rgenix, Inc. | Polymorphs and uses thereof |
AU2020401286A1 (en) | 2019-12-13 | 2022-06-23 | Inspirna, Inc. | Metal salts and uses thereof |
CN110981764A (zh) * | 2019-12-25 | 2020-04-10 | 郑州轻工业大学 | 3-环丙基-n-苯基苯磺酰胺及其制备方法 |
CN111018752A (zh) * | 2019-12-25 | 2020-04-17 | 郑州轻工业大学 | 一种对位环丙烷基取代的苯磺酰苯胺及其制备方法 |
CN111056979A (zh) * | 2019-12-25 | 2020-04-24 | 郑州轻工业大学 | 3-环丙基苯磺酰苄胺及其合成方法 |
CN110938024A (zh) * | 2019-12-25 | 2020-03-31 | 郑州轻工业大学 | 2-环丙基-n-苄基苯磺酰胺及其制备方法 |
CN111018751A (zh) * | 2019-12-25 | 2020-04-17 | 郑州轻工业大学 | 邻环丙基苯磺酰苯胺及其制备方法 |
Family Cites Families (10)
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US6316503B1 (en) | 1999-03-15 | 2001-11-13 | Tularik Inc. | LXR modulators |
US7482366B2 (en) * | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
AU2003233670A1 (en) | 2002-05-24 | 2003-12-12 | Pharmacia Corporation | Sulfone liver x-receptor modulators |
BR0311263A (pt) | 2002-05-24 | 2005-04-26 | Pharmacia Corp | Moduladores anilino receptores-x do fìgado |
GB0215650D0 (en) * | 2002-07-05 | 2002-08-14 | Cyclacel Ltd | Bisarylsufonamide compounds |
US7786165B2 (en) * | 2004-03-15 | 2010-08-31 | Takeda Pharmaceutical Company Limited | Aminophenylpropanoic acid derivative |
FR2869904B1 (fr) * | 2004-05-07 | 2006-07-28 | Fournier S A Sa Lab | Modulateurs des recepteurs lxr |
US20060135773A1 (en) * | 2004-06-17 | 2006-06-22 | Semple Joseph E | Trisubstituted nitrogen modulators of tyrosine phosphatases |
EP1917233B1 (en) * | 2005-08-25 | 2008-12-17 | SmithKline Beecham Corporation | Anilinohexafluoroisopropanol compounds |
JP2007314516A (ja) * | 2006-04-25 | 2007-12-06 | Daiichi Sankyo Co Ltd | 2以上の置換基を有するベンゼン化合物を含有する医薬 |
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CN101808983B (zh) | 2013-11-13 |
WO2009040289A2 (en) | 2009-04-02 |
JP2010540482A (ja) | 2010-12-24 |
MX2010003224A (es) | 2010-04-01 |
BRPI0817262A2 (pt) | 2015-06-16 |
WO2009040289A3 (en) | 2009-06-04 |
KR20100065195A (ko) | 2010-06-15 |
KR101240809B1 (ko) | 2013-03-07 |
CN101808983A (zh) | 2010-08-18 |
US8039493B2 (en) | 2011-10-18 |
EP2205556A2 (en) | 2010-07-14 |
AU2008303601A1 (en) | 2009-04-02 |
US20090088459A1 (en) | 2009-04-02 |
JP5307143B2 (ja) | 2013-10-02 |
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